US4032325A - Method for controlling weeds with amino acid higher alkyl esters - Google Patents
Method for controlling weeds with amino acid higher alkyl esters Download PDFInfo
- Publication number
- US4032325A US4032325A US05/514,745 US51474574A US4032325A US 4032325 A US4032325 A US 4032325A US 51474574 A US51474574 A US 51474574A US 4032325 A US4032325 A US 4032325A
- Authority
- US
- United States
- Prior art keywords
- acid
- ester hydrochloride
- weeds
- group
- active compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aldehyde or keto groups, or thio analogues thereof, directly attached to an aromatic ring system, e.g. acetophenone; Derivatives thereof, e.g. acetals
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
Definitions
- This invention relates to a herbicidal composition of an amino acid higher alkyl ester type which has an excellent weed controlling effect, especially a germination inhibitory activity and a herbicidal activity, and which exhibits a markedly reduced toxicity on man, poultry, domestic animals, fish and other non-mammalian aquatic animals and also a reduced residual toxicity in soil; and to a method for controlling weeds.
- the herbicidal composition of this invention is useful for controlling weeds growing in various loci such as fields, paddies, orchards, forests and gardens, but can be applied especially preferably to post-emergence weed control for agriculture and horticulture in fields, paddies and orchards, especially for controlling weeds in paddies.
- Active compounds of the carbamate, acid amide, diphenylether, s-triazine, urea and dipyridyl types have previously been used as herbicides against weeds in fields and paddies, but these conventional herbicides have not been entirely satisfactory in respect of residual toxicity in soil and toxicity on man, poultry, domestic animals, fish and other non-mammalian aquatic animals. Thus, their use has been limited because of the need to control pollution.
- an active compound selected from the group consisting of acid addition salts of higher alkyl esters of amino acids, preferably those in which the alkyl group contains 8 to 22 carbon atoms, acid addition salts of N-lower alkyl substitution products of said alkyl esters, preferably those in which the lower alkyl group contains 1 to 4 carbon atoms, and quaternary ammonium salts of N-lower alkyl substitution products of said alkyl esters exhibits an excellent germination inhibitory activity and a herbicidal activity on broadleaf weeds in the paddy field such as barnyard-grass (Echinochloa oryzicola VASING), Monachoria vaginalis PRESL, Eleocharis acicularis ROEM et SHULT, and Cyperus difformis L.
- an active compound selected from the group consisting of acid addition salts of higher alkyl esters of amino acids, preferably those in which the alkyl group contains 8 to 22 carbon atoms, acid addition salt
- upland weeds such as Digifaria adscendens HENR, or Amaranthus viridis L. without causing such a pollution problem. It has also been found that the above active compounds exhibit an outstanding effect within a very short period of time, for example, within 2 to 3 days, against broadleaf weeds in paddy fields, the effect being not reduced even in a flooded paddy field, and has no phytotoxicity on rice plants, and further that the compound exhibits an excellent herbicidal activity on the above upland weeds without phytotoxicity on plants cultivated in upland.
- the active compound in the herbicidal composition of this invention is selected from the group consisting of acid addition salts of higher alkyl esters, preferably C 8-22 higher alkyl esters, of amino acids, acid addition salts of N-lower alkyl substitution products, preferably C 1-4 lower alkyl substitution products, of said esters, and quaternary ammonium salts of N-lower alkyl substitution products of said esters.
- Preferred active compounds are, for example, those of the following formulae (1) and (2).
- R 1 is a member selected from the group consisting of a hydrogen atom, alkyl groups containing 1 to 4 carbon atoms, ##STR2## and H 2 N.(CH 2 ) 4 ;
- R 2 is an alkyl group containing 8 to 22 carbon atoms;
- Y is a hydrogen atom or methyl group;
- R 3 and R 4 are each a member of the group consisting of a hydrogen atom and a methyl group;
- Z is an inorganic or organic acid group; and n is 0 or an integer of 1 to 5, and when n is an integer of 1 to 5, both of R 1 and Y are hydrogen atoms; ##STR3## wherein Y and R 2 are the same as defined with respect to formula (1).
- amino acids such as ⁇ -amino acid, ⁇ -amino acid, and ⁇ -amino acid can be utilized as the amino acid component of the compounds of formula (1) and (2) above.
- preferred amino acids are glycine, alanine, ⁇ -alanine, valine, norvaline, leucine, isoleucine, norleucine, tyrosine, threonine, 2-aminoisobutyric acid, 6-aminocaproic acid, lysine, and arginine, and N--C 1-4 alkyl substitution products, such as N-methyl or N-ethyl substitution products, of these, such as glycine betaine, N,N'-dimethylvaline, and N,N'-dimethylalanine.
- the amino acids may be optically active ones or racemic modifications.
- ester portion of the above preferred compounds of formulae (1) and (2) are esters of straight chain or branched alkyls containing 8 to 22 carbon atoms such as octyl, decyl, lauryl, myristyl, cetyl, stearyl, 2-hexyldecyl and 2-octyldecyl esters. Of these, the decyl and lauryl esters are preferred.
- Both organic acids and inorganic acids can be utilized as the acid group Z which forms an acid addition salt in the formula (1).
- preferred acids are hydrochloric acid, acetic acid, p-toluenesulfonic acid, oxalic acid, and pyroglutamic acid.
- the solubility of the active component used in this invention differs according to the type of the acid addition salt, the number of carbon atoms of the alkyl esters, etc., but generally, it is water-soluble. Where the solubility of the active ingredient is very low, it is preferred to utilize a suitable dispersing agent.
- the active ingredient used in this invention can be used conjointly with other known herbicides or fungicides.
- the conjoint use of it with a known herbicide, 3,3'-dimethyl-4-methoxybenzophenone has been found to exhibit a unique synergistic effect.
- the 3,3'-dimethyl-4-methoxybenzophenone has an excellent herbicidal effect when applied in the pre-emergence stage, but does not show a satisfactory herbicidal effect when applied in the post-emergence stage.
- this 3,3'-dimethyl-4-methoxybenzophenone is used in admixture with the active ingredient used in the present invention, the mixture shows an excellent synergistic herbicidal effect in post-emergence application.
- the active compound (A) of this invention and the 3,3'-dimethyl-4-methoxybenzophenone (B) are used in an (A):(B) weight ratio of 2:8 to 8:2, more preferably 4:6 to 6:4.
- the herbicidal composition of this invention can be formulated in any desired formulation such as dust, granule, pellet, wettable powder, emulsifiable concentrate or dispersed liquid using various solid and liquid diluent or carriers known in the art.
- solid diluents or carriers are clay, white carbon, bentonite, kaolin, diatomaceous earth, starch, and gum arabic, with or without a dispersing agent or emulsifier.
- liquid diluents or carriers are water, water containing a dispersing agent or emulsifier, dioxane, isophorone or ethanol.
- the above-mentioned dispersing agent or emulsifier may, for example, be soap, sulfuric acid esters of higher alcohols, alkylsulfonate salts, quaternary ammonium salts, polyalkylene oxides, polyoxyalkylene ethers, or alkali metals or calcium salts of ligninsulfonic acid.
- the amount of the above diluent or carrier to be used in the composition of this invention can be suitably selected, and for example, the content of the active compound (including a mixture of the active compounds) can be about 1 to about 99% by weight based on the weight of the herbicidal composition.
- the amount of the active compound can be suitably selected also according to the type of formulation. For example, the amount may be about 10 to about 90% by weight in the case of emulsifiable concentrate, suspension or wettable powder, and it may be frequently about 10 to about 30% by weight when the formulation is granule or pellet.
- a method for controlling weeds which comprises applying to weeds or the locus where weeds are growing or will grow a herbicidal amount of an active compound selected from the group consisting of acid addition salts of higher alkyl esters of amino acids, acid addition salts of N-lower alkyl substitution products of said esters and quaternary ammonium salts of N-lower alkyl substitution products of said esters.
- the active compound can be applied as a mixture of it with a known herbicide, 3,3'-dimethyl-4-methoxybenzophenone.
- the application of the herbicidal composition of this invention is preferably done in the post-emergence stage.
- the composition is applied to weeds in paddies desirably in the early stage of germination.
- the herbicidal composition of this invention exhibits an excellent herbicidal effect without causing phytotoxicity even when applied to the period of growth of weeds after rice plant seedlings have been transplanted in paddies.
- a foliar treatment of weeds with the herbicidal composition of this invention gives good results.
- the rate of application of the active ingredients can be suitably varied according to the time of application, the type of weeds, the type of the active compound, and the type of formulation.
- the rate of the herbicidal composition to be applied is about 50 to about 100 g per are.
- amounts of about 100 to about 400 g per are employed in the case of upland weeds, and about 50 to about 150 g per are in the case of weeds in paddies.
- the preferred amount of the mixture is about 30 to about 60 g per are.
- Glycine lauryl ester DL-pyroglutamate (20 parts), 2 parts of white carbon, 2 parts of sodium ligninsulfonate, 4 parts of a polyoxyethylene alkyl ether and 72 parts of clay were mixed and pulverized to form 100 parts of a wettable powder.
- DL-valine lauryl ester hydrochloride (10 parts), 15 parts of starch, 72 parts of bentonite and 3 parts of a sodium salt of lauryl alcohol sulfate ester were mixed and pulverized to form 100 parts of granules.
- Betaine lauryl ester hydrochloride 50 parts
- 10 parts of an emulsifier SORPOL, a registered tradename for a product of Toho Chemical Co., Ltd., Japan
- 40 parts of water were mixed to form 100 parts of an emulsifiable concentrate.
- Soil from a rice paddy field was filled in synthetic resin pots each having an inside diameter of 8 cm, and seeds of rice plant (Nihonbare variety), barnyard grass (Echinochloa oryzicola VASING), Monochoria vaginalis PRESL., and other broad-leaf weeds were sown. Then, the pots were irrigated so that the depth of water became 3 cm. Then, at the stage where the first leaves sprouted (in the case of barnyard grass) and at the stage of growth (the other weeds), these weeds were treated with an aqueous solution of the active ingredient in the amount indicated in Table 1 (those not soluble in water were first dissolved in dioxane and then in water). Ten days after the treatment, the treated pots were examined for a herbicidal effect and the state of growth of the weeds. The results are shown in Table 1 according to the following scale of evaluation.
- a chain link was placed in the lower layer of Wagner pots (1/5000 are), and pebbles and sand were successively packed onto it.
- Soil of a rice paddy was filled in the pots as an upper layer.
- a cock was fixed to the discharge opening at the bottom of the pot so that water at a desired flow rate could be discharged from the pot.
- Seeds of barnyard grass (Echinochloa oryzicola VASHING), Monochoria vaginalis PRESL., and other broadleaved weeds were sown, and at the same time, rice plant seedlings (Nihonbare variety) were transplanted in the pots.
- the active compounds in accordance with this invention exhibited a high herbicidal effect even when used in a flooded paddy field on the 3rd to the 10th day after the transplantation, and caused no phytotoxicity on rice plants.
- the above ingredients were mixed and pulverized to form 100 parts of a wettable powder.
- the above ingredients were mixed uniformly, and granulated to form 100 parts of granules.
- Example shows the control effect of the compounds of formula (2) against upland weeds.
- Soil from fields was filled in synthetic resin pots each having an inside diameter of 8 cm, and seeds of barnyard grass, Amaranthus viridis L. and Digitaria adscendens HENR. were sown.
- an aqueous solution of each of the effective components in a prescribed amount was sprayed on the leaves of the weeds in an amount of 10 ml. per pot using a spray gun.
- the state of growth was observed on the 7th day from the treatment, and the herbicidal effect was shown on the same scale as used in Example 4. The results are shown in Table 5 below.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
A herbicidal composition comprising a herbicidal amount of an active compound selected from the group consisting of acid addition salts of higher alkyl esters of amino acids, acid addition salts of N-lower alkyl substitution products of said esters and quaternary ammonium salts of N-lower alkyl substitution products of said esters, and a diluent or carrier, and a method for controlling weeds using said herbicidal composition.
Description
This invention relates to a herbicidal composition of an amino acid higher alkyl ester type which has an excellent weed controlling effect, especially a germination inhibitory activity and a herbicidal activity, and which exhibits a markedly reduced toxicity on man, poultry, domestic animals, fish and other non-mammalian aquatic animals and also a reduced residual toxicity in soil; and to a method for controlling weeds.
The herbicidal composition of this invention is useful for controlling weeds growing in various loci such as fields, paddies, orchards, forests and gardens, but can be applied especially preferably to post-emergence weed control for agriculture and horticulture in fields, paddies and orchards, especially for controlling weeds in paddies.
Active compounds of the carbamate, acid amide, diphenylether, s-triazine, urea and dipyridyl types have previously been used as herbicides against weeds in fields and paddies, but these conventional herbicides have not been entirely satisfactory in respect of residual toxicity in soil and toxicity on man, poultry, domestic animals, fish and other non-mammalian aquatic animals. Thus, their use has been limited because of the need to control pollution.
The inventors of the present application have been engaged in the development of herbicides which exhibit an excellent herbicidal effect without posing any such pollution problem. As a result, they found that an active compound selected from the group consisting of acid addition salts of higher alkyl esters of amino acids, preferably those in which the alkyl group contains 8 to 22 carbon atoms, acid addition salts of N-lower alkyl substitution products of said alkyl esters, preferably those in which the lower alkyl group contains 1 to 4 carbon atoms, and quaternary ammonium salts of N-lower alkyl substitution products of said alkyl esters exhibits an excellent germination inhibitory activity and a herbicidal activity on broadleaf weeds in the paddy field such as barnyard-grass (Echinochloa oryzicola VASING), Monachoria vaginalis PRESL, Eleocharis acicularis ROEM et SHULT, and Cyperus difformis L. and upland weeds such as Digifaria adscendens HENR, or Amaranthus viridis L. without causing such a pollution problem. It has also been found that the above active compounds exhibit an outstanding effect within a very short period of time, for example, within 2 to 3 days, against broadleaf weeds in paddy fields, the effect being not reduced even in a flooded paddy field, and has no phytotoxicity on rice plants, and further that the compound exhibits an excellent herbicidal activity on the above upland weeds without phytotoxicity on plants cultivated in upland.
It is therefore an object of this invention to provide a herbicidal composition of an amino acid higher alkyl ester type herbicidal composition having an excellent herbicidal effect and causing no pollution problem with its markedly reduced toxicity on man, domestic animals, poultry, fish and other non-mammalian aquatic animals and also a markedly reduced residual toxicity in soil; and a method for weed control using this composition.
The active compound in the herbicidal composition of this invention is selected from the group consisting of acid addition salts of higher alkyl esters, preferably C8-22 higher alkyl esters, of amino acids, acid addition salts of N-lower alkyl substitution products, preferably C1-4 lower alkyl substitution products, of said esters, and quaternary ammonium salts of N-lower alkyl substitution products of said esters. Preferred active compounds are, for example, those of the following formulae (1) and (2). ##STR1## wherein R1 is a member selected from the group consisting of a hydrogen atom, alkyl groups containing 1 to 4 carbon atoms, ##STR2## and H2 N.(CH2)4 ; R2 is an alkyl group containing 8 to 22 carbon atoms; Y is a hydrogen atom or methyl group; R3 and R4 are each a member of the group consisting of a hydrogen atom and a methyl group; Z is an inorganic or organic acid group; and n is 0 or an integer of 1 to 5, and when n is an integer of 1 to 5, both of R1 and Y are hydrogen atoms; ##STR3## wherein Y and R2 are the same as defined with respect to formula (1).
Various amino acids such as α-amino acid, β-amino acid, and ω-amino acid can be utilized as the amino acid component of the compounds of formula (1) and (2) above. Examples of preferred amino acids are glycine, alanine, β-alanine, valine, norvaline, leucine, isoleucine, norleucine, tyrosine, threonine, 2-aminoisobutyric acid, 6-aminocaproic acid, lysine, and arginine, and N--C1-4 alkyl substitution products, such as N-methyl or N-ethyl substitution products, of these, such as glycine betaine, N,N'-dimethylvaline, and N,N'-dimethylalanine. The amino acids may be optically active ones or racemic modifications.
Examples of the ester portion of the above preferred compounds of formulae (1) and (2) are esters of straight chain or branched alkyls containing 8 to 22 carbon atoms such as octyl, decyl, lauryl, myristyl, cetyl, stearyl, 2-hexyldecyl and 2-octyldecyl esters. Of these, the decyl and lauryl esters are preferred.
Both organic acids and inorganic acids can be utilized as the acid group Z which forms an acid addition salt in the formula (1). Examples of preferred acids are hydrochloric acid, acetic acid, p-toluenesulfonic acid, oxalic acid, and pyroglutamic acid.
The solubility of the active component used in this invention differs according to the type of the acid addition salt, the number of carbon atoms of the alkyl esters, etc., but generally, it is water-soluble. Where the solubility of the active ingredient is very low, it is preferred to utilize a suitable dispersing agent.
The active ingredient used in this invention can be used conjointly with other known herbicides or fungicides. The conjoint use of it with a known herbicide, 3,3'-dimethyl-4-methoxybenzophenone has been found to exhibit a unique synergistic effect. The 3,3'-dimethyl-4-methoxybenzophenone has an excellent herbicidal effect when applied in the pre-emergence stage, but does not show a satisfactory herbicidal effect when applied in the post-emergence stage. When this 3,3'-dimethyl-4-methoxybenzophenone is used in admixture with the active ingredient used in the present invention, the mixture shows an excellent synergistic herbicidal effect in post-emergence application. It may be recommended that the active compound (A) of this invention and the 3,3'-dimethyl-4-methoxybenzophenone (B) are used in an (A):(B) weight ratio of 2:8 to 8:2, more preferably 4:6 to 6:4.
The herbicidal composition of this invention can be formulated in any desired formulation such as dust, granule, pellet, wettable powder, emulsifiable concentrate or dispersed liquid using various solid and liquid diluent or carriers known in the art. Examples of solid diluents or carriers are clay, white carbon, bentonite, kaolin, diatomaceous earth, starch, and gum arabic, with or without a dispersing agent or emulsifier. Examples of liquid diluents or carriers are water, water containing a dispersing agent or emulsifier, dioxane, isophorone or ethanol. The above-mentioned dispersing agent or emulsifier may, for example, be soap, sulfuric acid esters of higher alcohols, alkylsulfonate salts, quaternary ammonium salts, polyalkylene oxides, polyoxyalkylene ethers, or alkali metals or calcium salts of ligninsulfonic acid.
The amount of the above diluent or carrier to be used in the composition of this invention can be suitably selected, and for example, the content of the active compound (including a mixture of the active compounds) can be about 1 to about 99% by weight based on the weight of the herbicidal composition. The amount of the active compound can be suitably selected also according to the type of formulation. For example, the amount may be about 10 to about 90% by weight in the case of emulsifiable concentrate, suspension or wettable powder, and it may be frequently about 10 to about 30% by weight when the formulation is granule or pellet.
According to this invention, there can be provided a method for controlling weeds, which comprises applying to weeds or the locus where weeds are growing or will grow a herbicidal amount of an active compound selected from the group consisting of acid addition salts of higher alkyl esters of amino acids, acid addition salts of N-lower alkyl substitution products of said esters and quaternary ammonium salts of N-lower alkyl substitution products of said esters. The active compound can be applied as a mixture of it with a known herbicide, 3,3'-dimethyl-4-methoxybenzophenone.
The application of the herbicidal composition of this invention is preferably done in the post-emergence stage. For example, the composition is applied to weeds in paddies desirably in the early stage of germination. As will be shown later in the Examples, the herbicidal composition of this invention exhibits an excellent herbicidal effect without causing phytotoxicity even when applied to the period of growth of weeds after rice plant seedlings have been transplanted in paddies. In order to control upland weeds, a foliar treatment of weeds with the herbicidal composition of this invention gives good results.
The rate of application of the active ingredients can be suitably varied according to the time of application, the type of weeds, the type of the active compound, and the type of formulation. Generally, the rate of the herbicidal composition to be applied is about 50 to about 100 g per are. Often, amounts of about 100 to about 400 g per are are employed in the case of upland weeds, and about 50 to about 150 g per are in the case of weeds in paddies. When a mixture of the active compound and 3,3'-dimethyl-4-methoxybenzophenone is used, the preferred amount of the mixture is about 30 to about 60 g per are.
Examples of the herbicide of this invention are shown below. All parts in the Examples are by weight.
Glycine lauryl ester DL-pyroglutamate (20 parts), 2 parts of white carbon, 2 parts of sodium ligninsulfonate, 4 parts of a polyoxyethylene alkyl ether and 72 parts of clay were mixed and pulverized to form 100 parts of a wettable powder.
DL-valine lauryl ester hydrochloride (10 parts), 15 parts of starch, 72 parts of bentonite and 3 parts of a sodium salt of lauryl alcohol sulfate ester were mixed and pulverized to form 100 parts of granules.
Betaine lauryl ester hydrochloride (50 parts), 10 parts of an emulsifier (SORPOL, a registered tradename for a product of Toho Chemical Co., Ltd., Japan) and 40 parts of water were mixed to form 100 parts of an emulsifiable concentrate.
The control effect of the herbicide of this invention against weeds in paddies and upland weeds will be described below.
Treatment of irrigated soil:
Soil from a rice paddy field was filled in synthetic resin pots each having an inside diameter of 8 cm, and seeds of rice plant (Nihonbare variety), barnyard grass (Echinochloa oryzicola VASING), Monochoria vaginalis PRESL., and other broad-leaf weeds were sown. Then, the pots were irrigated so that the depth of water became 3 cm. Then, at the stage where the first leaves sprouted (in the case of barnyard grass) and at the stage of growth (the other weeds), these weeds were treated with an aqueous solution of the active ingredient in the amount indicated in Table 1 (those not soluble in water were first dissolved in dioxane and then in water). Ten days after the treatment, the treated pots were examined for a herbicidal effect and the state of growth of the weeds. The results are shown in Table 1 according to the following scale of evaluation.
Table 1
______________________________________
Rate Herbicidal Effect
(Active Echino- Mona-
ingredi- chloa choria Broad-
Cyperus
Compound
ent) oryzicola vaginalis
leaf difformis
No. g/a VASING PRESL weed L.
______________________________________
1* 100 3 2 4 4
2 100 3 2 4 4
50 3 2 4 3
3 100 4 2 4 2
50 3 2 4 2
4 100 4 4 4 4
50 4 4 4 4
25 3 3 3 3
5 100 4 2 4 3
6 100 3 1 3 3
7* 100 3 2 3 3
8 100 4 2 4 3
9 100 4 4 4 4
50 4 4 4 4
25 3 3 3 3
10 100 3 1 2 2
11 100 2 2 1 2
12 100 2 2 2 2
13 100 2 2 2 2
14 100 2 2 2 2
15 100 2 3 3 2
16 100 2 2 2 2
______________________________________
Note
1* N,N-dimethyl-DL-valinelauryl ester
2 Glycine lauryl ester
3 DL-alaninelauryl ester
4 DL-valinelauryl ester hydrochloride
5 DL-leucinelauryl ester
6 Glycinedecyl ester hydrochloride
7* DL-tyrosine lauryl ester
8 DL-threoninedecyl ester
9 2-aminoisobutyric acid lauryl ester
10 DL-lysine lauryl ester
11 Betaine lauryl ester hydrochloride
12 DL-aspartic acid lauryl ester
13 DL-glutamic acid lauryl ester
14 DL-tyrosine lauryl ester
15 DL-alanine lauryl ester oxalate
16 ε-Aminocaproic acid lauryl ester DL-pyroglutamate
[*insoluble in water (dissolved in water after having been dissolved in
dioxane)
Herbicidal effect:
0: none
1: slight
2: ordinary
3: strong
4: the weeds were withered
Herbicidal effect on various weeds in paddies:
The following plants (unless otherwise specified, they were all in the 5-leaf stage) were transplanted in synthetic resin pots each having an inside diameter of 12 cm. The pots were irrigated to a water depth of 4 cm. After these plants rooted (7 days later), they were treated with a chemical liquid containing a predetermined amount of the active ingredient dissolved therein. The plants were examined 6 days after the treatment. The standard of evaluation was the same as in Example 4.
Table 2
__________________________________________________________________________
(Weeding spectrum)
Herbicidal effect
Compound
2 3 4 4 5 9 9
Weeds
g/a
No. 200 200 200 100 200 200 100
__________________________________________________________________________
Lobelia chinensis
LOUR 4 4 4 4 4 4 4
Lindernia
procumbens PHILCOX
4 4 4 4 4 4 4
Vandellia
angustifolia BENTH
3 4 4 4 3 4 4
Dopatrium
junceum HAMILT
3 4 4 4 3 4 4
Ludwigia prostrata
ROXB. 4 4 4 4 4 4 4
Rotala indica
KOEHNE 4 4 4 4 4 4 4
Elatine triandra
SCHK 4 4 4 4 4 4 4
Callitriche
Verna L. 4 4 4 4 4 4 4
Monochoria
vaginalis PRESL.
3 4 4 4 3 4 4
Aneilema Keisak
HASSK. 2 2 2 2 2 2 2
Echinochloa
Oryzicola
VASING 4 4 4 4 4 4 4
Spirodela poly-
rhiza SCHLEID.
4 4 4 4 4 4 4
Lemna paucicostata
HEGELM 4 4 4 4 4 4 4
Potamogeton
distinctus A. BENN.
3 3 3 3 3 3 3
Cyperus difformis
L 4 4 4 4 4 4 4
Eleocharis
acicularis ROME
et SCHULT 3 3 4 3 4 3
__________________________________________________________________________
Note:
The compound numbers are the same as those described in the footnote to
Table 1.
Herbicidal activity in an overflooded condition:
A chain link was placed in the lower layer of Wagner pots (1/5000 are), and pebbles and sand were successively packed onto it. Soil of a rice paddy was filled in the pots as an upper layer. A cock was fixed to the discharge opening at the bottom of the pot so that water at a desired flow rate could be discharged from the pot. Seeds of barnyard grass (Echinochloa oryzicola VASHING), Monochoria vaginalis PRESL., and other broadleaved weeds were sown, and at the same time, rice plant seedlings (Nihonbare variety) were transplanted in the pots. At the beginning of growing of weeds (3 days after the transplantation) and at the stage of growth of the weeds (8 to 10 days after the transplantation), a chemical liquid containing a predetermined amount of the active ingredient dissolved therein was applied to the weeds. For 3 days after the treatment, the water was overflooded at a rate of 2 cm/day, and thereafter, the weeds were allowed to grow in an irrigated condition with a water depth of 3 cm. On the 24th day after the transplantation, the remaining weeds were pulled up, and their dry weight was measured. The weight was compared with that in a non-treated lot, and the rate of control was calculated according to the following equation, and the results are shown in Table 3. ##EQU1##
Table 3
______________________________________
Rate of control (%)
Echi-
no-
chloa Cy-
Treat- ory- Mona- perus Phy-
ing zi- choria dif- to-
Com- con- Flood- cola vagi- Broad-
form- tox-
pound di- ed VAS- nalis leaf is ici-
No. tions* water ING PRESL weed L ty
______________________________________
4 +3, - 90 100 100 60 -
100g/a + 80 100 100 90 -
+3, - 50 90 90 60 -
50g/a + 80 100 100 60 -
+3, - 30 100 80 80 -
25g/a + 90 100 90 60 -
+10, - 20 70 100 30 -
100g/a + 80 100 100 80 -
+10, - 10 70 80 10 -
50g/a + 80 90 90 60 -
+3, - 90 100 100 80 -
50g/a
+10, + 80 100 100 80 -
50g/a
9 +3, - 100 100 90 50 -
100g/a + 100 90 100 80 -
+3, - 100 90 90 70 -
50g/a + 100 90 90 30 -
+8, - 100 90 100 90 -
100g/a + 100 90 100 90 -
+8, - 30 80 100 80 -
50g/a + 100 90 100 80 -
______________________________________
Note:
The compound numbers were the same as those in Table 1.
* +3, +8 and +10 respectively mean that the treatment was performed on th
3rd, 8th and 10th day after the transplatation.
As demonstrated above, the active compounds in accordance with this invention exhibited a high herbicidal effect even when used in a flooded paddy field on the 3rd to the 10th day after the transplantation, and caused no phytotoxicity on rice plants.
Some examples of formulation of the mixed active ingredient will be shown below.
Dl-valine lauryl ester hydrochloride; 25 parts
3,3'-dimethyl-4-methoxybenzophenone; 25 parts
White carbon; 2 parts
Sodium ligninsulfonate; 2 parts
Polyoxyethylene alkyl ether; 4 parts
Clay; 42 parts
The above ingredients were mixed and pulverized to form 100 parts of a wettable powder.
Dl-valinelauryl ester hydrochloride; 7 parts
3,3'-dimethyl-4-methoxybenzophenone; 7 parts
Bentonite; 76 parts
Calcium ligninsulfonate; 10 parts
The above ingredients were mixed uniformly, and granulated to form 100 parts of granules.
Examples will further be given in order to illustrate the herbicidal effect of the mixed active ingredient against weeds in paddies.
Table 4
______________________________________
Amount
of
Chemi-
Rate of residual weeds (%)
cal Barnyard grass
(act. Be- 1 - Cy-
ive fore leaf 1.5 - perus
ingre- the to to dif-
dient one- 1.5 - 2 - Broad-
form-
Chemi- (g/ leaf leaf leaf leaved
is
cals are) stage stage stage grass L
______________________________________
No. 1 3.2 90 100 100 100 100
10 70 75 80 60 85
18 40 40 60 30 60
32 10 20 30 10 40
56 0 10 30 5 40
No. 2 3.2 80 90 100 70 95
10 40 70 85 50 80
18 10 40 45 20 50
32 0 10 10 10 30
56 0 0 5 0 30
No. 3 3.2 70 90 100 60 70
10 40 60 70 35 50
Single 18 10 40 40 20 50
com- 32 0 20 20 2 20
pound 56 0 0 0 0 20
No. 4 3.2 80 95 100 75 70
10 50 60 65 30 50
18 20 20 30 10 40
32 0 5 10 5 10
56 0 0 0 0 10
DMB 3.2 10 70 70 20 3
10 0 40 40 2 1
18 0 30 30 4 0
32 0 20 30 0 0
56 0 10 30 0 0
No. 1 18 0 10 15 0 0
DMB 18
Mix- No. 2 18 0 8 9 0 0
tures DMB 18
No. 3 18 0 8 15 0 0
DMB 10
No. 3 18 0 7 9 0 0
DMB 18
No. 3 18 0 0 7 0 0
DMB 18
No. 4 18
DMB 18 0 0 8 0 0
______________________________________
the following Example shows the control effect of the compounds of formula (2) against upland weeds.
Soil from fields was filled in synthetic resin pots each having an inside diameter of 8 cm, and seeds of barnyard grass, Amaranthus viridis L. and Digitaria adscendens HENR. were sown. At the 2- to 3-leaf stage, an aqueous solution of each of the effective components in a prescribed amount was sprayed on the leaves of the weeds in an amount of 10 ml. per pot using a spray gun. The state of growth was observed on the 7th day from the treatment, and the herbicidal effect was shown on the same scale as used in Example 4. The results are shown in Table 5 below.
Table 5
______________________________________
Herbicidal effect
Digitaria
Compound
Concentra- Barnyard Amaranthus
adscendens
No. tion (ppm) grass viridis L.
HENR.
______________________________________
1 1000 3 3 3
2000 3 4 3
2 1000 3 3 3
2000 4 4 4
3 1000 3 3 3
2000 3 4 3
______________________________________
Note:
No. 1: Betaine decylester
No. 2: Betaine lauryl ester
No. 3: Betaine myristyl ester hydrochloride
Claims (6)
1. A method for controlling Lobelia chinensis LOUR, Lindernia procumbens PHILCOX, Vandellia Angustifolia BENTH, Dopatrium junceum HAMILT, Ludwigia prostrata ROXB., Rotala indica KOEHNE, Elatine triandra SCHK, Callitriche Verna L., Monochoria vaginalis PRESL., Aneilema Keisak HASSK., Echinochloa Oryzicola VASING, Spirodela polyrhiza SCHLEID., Lemna paucicostata HEGELM, Potamogeton distinctus A. BENN., Cyperus difformis L, Eleocharis acicularis ROME et SCHULT, Amaranthus viridis L., or Digifaria adscendens HENR. weeds, which comprises applying to said weeds, or the locus where said weeds are growing or will grow, a herbicidal amount of an active compound selected from the group consisting of acid addition products of higher alkyl esters of amino acids, acid addition salts of N-lower alkyl substitution products of said esters and quaternary ammonium salts of N-lower alkyl substitution products of said esters wherein said active compound is selected from compounds of formula (1) ##STR4## wherein R1 is a member selected from the group consisting of a hydrogen atom, alkyl containing 1 to 4 carbon atoms, ##STR5## R2 is alkyl containing 8 to 22 carbon atoms, Y is a hydrogen atom or methyl, each of R3 and R4 is a member selected from the group consisting of a hydrogen atom and lower alkyl of 1 to 4 carbon atoms, Z is an inorganic or organic acid group selected from the group consisting of hydrochloric acid, acetic acid, p-toluene sulfonic acid, oxalic acid and pyroglutamic acid, n is 0 or an integer of 1 to 5 and, when an integer of 1 to 5, both R1 and Y are hydrogen atoms, and compounds of formula (2) ##STR6## wherein Y and R2 are the same as defined above.
2. The method of claim 1 wherein the rate of said active compound to be applied is 50 to 100 g per are.
3. The method of claim 1 wherein said active compound is selected from compounds of formula (1).
4. The method of claim 1 wherein said active compound is applied in the post-emergence stage.
5. The method of claim 1 wherein said active compound is selected from the group consisting of
N,n-dimethyl-DL-valinelauryl ester oxalate,
Glycine lauryl ester DL-pyroglutamate,
Dl-alaninelauryl ester hydrochloride,
Dl-valinelauryl ester hydrochloride,
Dl-leucinelauryl ester hydrochloride,
Glycinedecyl ester hydrochloride,
Dl-threoninedecyl ester hydrochloride,
2-aminoisobutyric acid lauryl ester hydrochloride,
Betaine lauryl ester hydrochloride,
Dl-alanine lauryl ester oxalate,
ε-aminocaproic acid lauryl ester DL-pyroglutamate,
Betaine decyl ester hydrochloride, and
Betaine myristyl ester hydrochloride.
6. The method of claim 1 wherein each of R3 and R4 is a member selected from the group consisting of a hydrogen atom and methyl.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/702,501 US4102672A (en) | 1973-10-19 | 1976-07-06 | Herbicidal composition of amino acid higher alkyl ester type and method for controlling weeds |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11831673A JPS531816B2 (en) | 1973-10-19 | 1973-10-19 | |
| JA48-118316 | 1973-10-19 | ||
| JP1805074A JPS50111235A (en) | 1974-02-14 | 1974-02-14 | |
| JA49-18050 | 1974-02-14 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US05/702,501 Division US4102672A (en) | 1973-10-19 | 1976-07-06 | Herbicidal composition of amino acid higher alkyl ester type and method for controlling weeds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US4032325A true US4032325A (en) | 1977-06-28 |
Family
ID=26354662
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US05/514,745 Expired - Lifetime US4032325A (en) | 1973-10-19 | 1974-10-15 | Method for controlling weeds with amino acid higher alkyl esters |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4032325A (en) |
| BR (1) | BR7408721D0 (en) |
| GB (1) | GB1455963A (en) |
| IT (1) | IT1049320B (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4980378A (en) * | 1988-06-01 | 1990-12-25 | Odontex, Inc. | Biodegradable absorption enhancers |
| US5082866A (en) * | 1988-06-01 | 1992-01-21 | Odontex, Inc. | Biodegradable absorption enhancers |
| WO1999001032A1 (en) * | 1997-07-03 | 1999-01-14 | Universite Du Quebec A Montreal | Method for improving the freezing tolerance of plants |
| US6083876A (en) * | 1996-06-14 | 2000-07-04 | Cultor Corporation | Effect of herbicides |
| CN112237069A (en) * | 2020-10-26 | 2021-01-19 | 中国科学院东北地理与农业生态研究所 | Method for transforming soda saline-alkali land waste fishpond into cattail wetland |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2290174A (en) * | 1940-10-04 | 1942-07-21 | Albert K Epstein | Bactericidal, germicidal, and antiseptic materials |
| US2888383A (en) * | 1956-09-12 | 1959-05-26 | Int Minerals & Chem Corp | Oral prophylactic compositions comprising a betaine derivative |
| US2965636A (en) * | 1958-01-15 | 1960-12-20 | Parke Davis & Co | Norleucine derivatives and process for producing same |
| US2965534A (en) * | 1958-04-21 | 1960-12-20 | Monsanto Chemicals | Inhibiting the growth of plant viruses |
| US3619168A (en) * | 1967-07-24 | 1971-11-09 | Emery Industries Inc | Method for killing undesirable plant growth |
| DE2203228A1 (en) * | 1971-01-23 | 1972-09-28 | Ajinomoto Kk | Fungicidal compositions for use in agriculture and horticulture |
| US3712804A (en) * | 1969-06-17 | 1973-01-23 | Oesterr Stickstoffwerke Ag | Composition for regulating the growth and metabolism of plants |
| US3736112A (en) * | 1970-03-31 | 1973-05-29 | Akzona Inc | Herbicidal compositions |
| US3758525A (en) * | 1969-04-01 | 1973-09-11 | Ajinomoto Kk | Process for preparing n-higher aliphatic acyl acidic amino acids |
-
1974
- 1974-10-08 IT IT28601/74A patent/IT1049320B/en active
- 1974-10-15 US US05/514,745 patent/US4032325A/en not_active Expired - Lifetime
- 1974-10-18 GB GB4532874A patent/GB1455963A/en not_active Expired
- 1974-10-18 BR BR8721/74A patent/BR7408721D0/en unknown
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2290174A (en) * | 1940-10-04 | 1942-07-21 | Albert K Epstein | Bactericidal, germicidal, and antiseptic materials |
| US2888383A (en) * | 1956-09-12 | 1959-05-26 | Int Minerals & Chem Corp | Oral prophylactic compositions comprising a betaine derivative |
| US2965636A (en) * | 1958-01-15 | 1960-12-20 | Parke Davis & Co | Norleucine derivatives and process for producing same |
| US2965534A (en) * | 1958-04-21 | 1960-12-20 | Monsanto Chemicals | Inhibiting the growth of plant viruses |
| US3619168A (en) * | 1967-07-24 | 1971-11-09 | Emery Industries Inc | Method for killing undesirable plant growth |
| US3758525A (en) * | 1969-04-01 | 1973-09-11 | Ajinomoto Kk | Process for preparing n-higher aliphatic acyl acidic amino acids |
| US3712804A (en) * | 1969-06-17 | 1973-01-23 | Oesterr Stickstoffwerke Ag | Composition for regulating the growth and metabolism of plants |
| US3736112A (en) * | 1970-03-31 | 1973-05-29 | Akzona Inc | Herbicidal compositions |
| DE2203228A1 (en) * | 1971-01-23 | 1972-09-28 | Ajinomoto Kk | Fungicidal compositions for use in agriculture and horticulture |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4980378A (en) * | 1988-06-01 | 1990-12-25 | Odontex, Inc. | Biodegradable absorption enhancers |
| US5082866A (en) * | 1988-06-01 | 1992-01-21 | Odontex, Inc. | Biodegradable absorption enhancers |
| US6083876A (en) * | 1996-06-14 | 2000-07-04 | Cultor Corporation | Effect of herbicides |
| WO1999001032A1 (en) * | 1997-07-03 | 1999-01-14 | Universite Du Quebec A Montreal | Method for improving the freezing tolerance of plants |
| CN112237069A (en) * | 2020-10-26 | 2021-01-19 | 中国科学院东北地理与农业生态研究所 | Method for transforming soda saline-alkali land waste fishpond into cattail wetland |
Also Published As
| Publication number | Publication date |
|---|---|
| BR7408721D0 (en) | 1975-08-05 |
| IT1049320B (en) | 1981-01-20 |
| GB1455963A (en) | 1976-11-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4123256A (en) | N-(4-substituted benzyloxy)phenyl)-N-methyl-N-methoxyurea | |
| US4146387A (en) | Synergistic herbicidal compositions | |
| US4488896A (en) | Methods and compositions for the selective control of undesirable weed species in the presence of wet-land crops | |
| US4032325A (en) | Method for controlling weeds with amino acid higher alkyl esters | |
| DD141257A5 (en) | PESTICIDES AND PLANT GROWTH-REGULATING COMPOSITIONS | |
| US4144049A (en) | N-(4-Benzyloxyphenyl)-N-methyl-N-methoxyurea | |
| EP0135838B1 (en) | 3-phenyl-4-methoxycarbonyl pyrazoles, process for their preparation and their use against plant growth | |
| US4102672A (en) | Herbicidal composition of amino acid higher alkyl ester type and method for controlling weeds | |
| US3999974A (en) | Barbituric acid derivatives | |
| AU608244B2 (en) | 4-substituted-2,6-diphenylpyridine derivatives, production of the same, and herbicide containing the same as an active ingredient | |
| HU176584B (en) | Herbicide preparation containing of active mateirals of two types | |
| US4272283A (en) | Herbicidal composition and method for controlling weeds | |
| SU784733A3 (en) | Herbicidic composition | |
| US3985539A (en) | 4,5-Dihalopyrrole-2-carbonitrile-containing terrestrial and aquatic hebicidal composition | |
| KR860002107B1 (en) | Method for preparing α, α-dimethylphenyl acetate anhydride derivative | |
| US4264777A (en) | Herbicidal diphenyl ether compound | |
| US3972707A (en) | N-(phenylcarbamoyl)-4-methylpiperidine herbicides compositions and herbicidal method | |
| US3996043A (en) | Triazine--antidote compositions and methods of use for cotton | |
| US3973945A (en) | Pyran-2,4-dione derivatives | |
| EP0107123B1 (en) | Aniline derivatives, process for their preparation and their use in combating undesired plant growth | |
| US4174210A (en) | Herbicidal and plant-growth regulating N-haloacetylphenylamino carbonyl oximes | |
| US5238909A (en) | 4-substituted isoxazole herbicides | |
| CA1158667A (en) | N-[2-(cyclopropyl)ethoxy]phenylanilide derivatives, and their production and use | |
| US3961935A (en) | Synergistic herbicidal composition comprising O-methyl or O-ethyl-O-(3-methyl-6-nitrophenyl)-N-secondary-butylphosphorothioamidate and a phenoxy-type herbicide | |
| CS214664B2 (en) | Herbicide means |